His moniker spells out exactly who he is. Yet Chance the Rapper's ascension has been anything but straightforward. Last year, Coloring Book became the first streaming-only release to chart on the Billboard 200 and be Grammy-nominated. And while lead single "No Problem" boasts of his refusal to sign to any label, Coloring Book's sheer joy, amplified by its gospel undertones, feels like its biggest act of rebellion. Here are five lesser-known facts about Chancelor Johnathan Bennett's curious ascension.

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Common was one of his earliest supporters.When Chance was still in high school, long before working with Kanye West, another Chicago hip-hop veteran gave his support. Chance's grandmother called in a favor to her neighbor: Common's grandmother. "You should have your grandson call my grandson," she said.

He once interned for Barack Obama.Obama first met Chance long before they sang together at the White House tree lighting. When Obama was a senator in Illinois, Chance's father, Ken Bennett, was his state director. Chance would intern with Obama during his first presidential campaign, and even spend a day phone banking on his behalf.

He went broke making Coloring Book.Chance has always released his music for free to reach as many people as possible. In the process, he has emptied his savings account for Surf, his collaborative album with Donnie Trumpet and the Social Experiment, then again for Coloring Book. "Like this studio is stupid expensive,” he said to GQ.

Kirk Franklin inspired Coloring Book's gospel bent.Two years ago Chance was renting a mansion in Los Angeles, on a perpetual Xanax high and miserable. So for days at 6 a.m., he'd blast Franklin's music to remind himself of happier days at church camp. "Finish Line/Drown" features the gospel titan alongside T-Pain, Noname and Eryn Allen Kane.

The smile Chance wears on Coloring Book is for his daughter.While he appears bewildered on 2012's 10 Day and 2013's Acid Rap, Chance knew he wanted to smile for Coloring Book's album art for the the sake of "black joy." "I thought, my best smile is probably when I'm holding my daughter," he during a discussion at the University of Chicago Institute of Politics. Kensli, also his first child, turns 17 months in February.